Dating my sister's friend

[Traveler78]

I was hoping for some advice and direction on this topic.

I'm interested in my sister's friend and I have a feeling she might be into me. I already asked my sister if it would bother her if I went out with her friend, to which I was given a green light! We've hung out in groups only a few times when I am with my sister (she lives out of state now) and she's been friends with my sister since High School (we're all in our early 30s now). I didn't have her phone number so I sent her a message on Facebook saying I thought we should hang out some time or see a movie and also gave her my #. She replied, "...Thanks for being so thoughtful, I will keep in touch..." and gave me her phone number and said she'll talk to me soon.

Should I feel like I need to approach this delicately as I've never dated any of my sister's friends before? We already know a little about each other so we're somewhat passed the "icebreaker" part. I'm looking for some advice on places to take her out for just a casual type encounter where there's no expectations and I can get a feel how she sees me.

Thanks!

[girl68]

call her? she gave you her number.

[adam95]

Yeah call her, plan a night out together. Something you'll both enjoy. do you know what she likes to do? Maybe go to a museum or an art gallery. No mushy romantic dinners yet though.
thats my opinion

[Traveler78]

I get free passes to the Museum of Modern Art and The Metropolitan Museum of Art in Manhattan from my job. Aside from that there's just wandering around Manhattan. Good Idea?

[adam95]

Yeah I think so. I don't think she'll feel uncomfortable considering you're not doing anything romantic yet.
But ask her if she's interested first. It would just be a major bore if she into that stuff (the art and museum stuff)

[Traveler78]

That's the beauty of Manhattan - so much to do in such a small space!

We're going to have to take the train into the city. She lives about 40 minutes from me, so I was curious if it would be good to meet in the city or go in together. The meet in the city has the benefit of ending the night casually and going separate ways immediately. Since the trains leave at specific times we'd have time to talk in the station then say our good night. Going in together we'd eventually end up either back at her place or mine for the other person's car. This might have some awkwardness?

[girl68]

I say let her come alone but ensure she gets home safely. Either advise her to call when she's home safe (call if she doesn't) or see her home and go home yourself. Do the "gentlemanly" thing.

[kitkitkitty]

the museum sounds like a great idea. if she's never gone before, buy her a little souvenier so she'll think of you every time she sees it

[Raze]

the museum sounds like a great idea. if she's never gone before, buy her a little souvenier so she'll think of you every time she sees it

Good idea!

[adam95]

Yeah it won't be awkward if you don't make it awkward. But if you're uncomfortable then do what girl68 says and just tell her to give you a miss call or something when shes reached home.

[Traveler78]

the museum sounds like a great idea. if she's never gone before, buy her a little souvenier so she'll think of you every time she sees it

Awesome idea!

[craigmarsh]

Call her out... Give her a bunch of flowers and chocolates make a close relationship then she itself will give her number..





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[kitkitkitty]

Call her out... Give her a bunch of flowers and chocolates make a close relationship then she itself will give her number..

1. he already has her number
2. he shouldn't go too OTT which is why we've suggested the museum.

[vashti]

If she's in her 30s, forget the souvenir, and buy her lunch.

[Traveler78]

Call her out... Give her a bunch of flowers and chocolates make a close relationship then she itself will give her number..

Like kitty mentioned, that's too OTT for what I'm looking to achieve initially.

If she's in her 30s, forget the souvenir, and buy her lunch.

I can do both, right? Sushi is planned for the after-museum meal. If she's tired from walking around the museum and doesn't want to go around the city then I think there's a Jennifer Aniston movie that comes out Friday or a Jazz Club.

Also, is it required that the souvenir be cool but a little cheezy? Like a badass refrigerator magnet?